Ginsenoside B2

Details

• Internal ID: 7d4be63c-c54c-481f-8c07-8a57209c6697
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CC4(C(CC(C5C4(CCC5C(C)(CCC=C(C)C)OC6C(C(C(C(O6)CO)O)O)O)C)O)C7(C3C(C(CC7)O)(C)C)C)C)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3C[C@@]4([C@H](C[C@H]([C@H]5[C@]4(CC[C@@H]5[C@](C)(CCC=C(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)[C@@]7([C@@H]3C([C@H](CC7)O)(C)C)C)C)CO)O)O)O)O)O
• InChI: InChI=1S/C48H82O18/c1-21(2)11-10-14-48(9,66-42-38(60)35(57)32(54)26(19-49)63-42)23-12-16-46(7)30(23)24(51)17-28-45(6)15-13-29(52)44(4,5)40(45)25(18-47(28,46)8)62-43-39(36(58)33(55)27(20-50)64-43)65-41-37(59)34(56)31(53)22(3)61-41/h11,22-43,49-60H,10,12-20H2,1-9H3/t22-,23-,24+,25-,26+,27+,28+,29-,30-,31-,32+,33+,34+,35-,36-,37+,38+,39+,40-,41-,42-,43+,45+,46+,47+,48-/m0/s1
• InChI Key: PWAOOJDMFUQOKB-WCZZMFLVSA-N
• Popularity: 202 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₂O₁₈
• Molecular Weight: 947.20 g/mol
• Exact Mass: 946.55011576 g/mol
• Topological Polar Surface Area (TPSA): 298.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): -0.03
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 12

Synonyms

• 52286-59-6
• Ginsenoside B2
• Panaxoside RE
• ginsenoside-Re
• Sanchinoside Re
• Chikusetsusaponin IVc
• UNII-46F3R0BL3I
• NSC 308877
• NSC-308877
• 46F3R0BL3I
• CHEBI:77148
• (20S)-ginsenoside Re
• EINECS 257-814-6
• 51542-56-4
• CHEMBL510095
• 2-O-(6-Deoxy-alpha-L-mannopyranosyl)-(3beta,6alpha,12beta)-20-(beta-D-glucopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl-beta-D-glucopyranoside
• MFCD00133369
• (3beta,6alpha,12beta)-20-(beta-D-glucopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
• (3beta,6alpha,12beta)-20-(beta-D-glucopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside
• C48H82O18
• C48-H82-O18
• Ginsenoside B2; Panaxoside Re; Sanchinoside Re
• GINSENOSIDE RE [INCI]
• SCHEMBL669738
• PWAOOJDMFUQOKB-WCZZMFLVSA-N
• DTXSID801317298
• EX-A6794
• HY-N0044
• BDBM50378779
• s3811
• AKOS025310861
• CCG-270589
• CS-3838
• DB14815
• AC-33946
• G0551
• C08944
• A829010
• Q27105064
• GINSENOSIDE RE (CONSTITUENT OF AMERICAN GINSENG, ASIAN GINSENG, AND TIENCHI GINSENG)
• .BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,6.ALPHA.,12.BETA.)-20-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,12-DIHYDROXYDAMMAR-24-EN-6-YL 2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-
• b-D-Glucopyranoside,(3b,6a,12b)-20-(b-D-glucopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl 2-O-(6-deoxy-a-L-mannopyranosyl)-
• beta-D-Glucopyranoside, (3beta,6alpha,12beta)-20-(beta-D-glucopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-
• GINSENOSIDE RE (CONSTITUENT OF AMERICAN GINSENG, ASIAN GINSENG, AND TIENCHI GINSENG) [DSC]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8885	88.85%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8312	83.12%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.5216	52.16%
P-glycoprotein inhibitior	+	0.7718	77.18%
P-glycoprotein substrate	-	0.5614	56.14%
CYP3A4 substrate	+	0.7305	73.05%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	+	0.6774	67.74%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9059	90.59%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.7554	75.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8144	81.44%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7957	79.57%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7629	76.29%
Androgen receptor binding	+	0.7409	74.09%
Thyroid receptor binding	-	0.5406	54.06%
Glucocorticoid receptor binding	+	0.6571	65.71%
Aromatase binding	+	0.6522	65.22%
PPAR gamma	+	0.7699	76.99%
Honey bee toxicity	-	0.5399	53.99%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9172	91.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.80%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.64%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.36%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.51%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.96%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.67%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.90%	92.94%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.56%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.53%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.51%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.49%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.83%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	87.65%	91.49%
CHEMBL1937	Q92769	Histone deacetylase 2	85.76%	94.75%
CHEMBL1977	P11473	Vitamin D receptor	84.39%	99.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.28%	89.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.16%	95.58%
CHEMBL1914	P06276	Butyrylcholinesterase	83.92%	95.00%
CHEMBL259	P32245	Melanocortin receptor 4	83.80%	95.38%
CHEMBL2581	P07339	Cathepsin D	82.69%	98.95%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.46%	96.90%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	82.39%	92.86%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.90%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.59%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.42%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.62%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.28%	95.83%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	80.04%	100.00%

Plants that contains it

• Aralia elata
• Luffa aegyptiaca
• Panax ginseng
• Panax japonicus
• Panax notoginseng
• Panax pseudoginseng
• Panax quinquefolius
• Panax trifolius
• Panax vietnamensis

Cross-Links

• PubChem: 441921
• NPASS: NPC208594
• LOTUS: LTS0083845
• wikiData: Q27105064